NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	254.634
LogP:	2.926
LogD:	3.08
LogS:	-3.446
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	5.04
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.518
MDCK Permeability:	2.7252879590378143e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.091
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.294
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	54.59601593017578%
Volume Distribution (VD):	2.294
Pgp-substrate:	44.22983932495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.356
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.236
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	9.904
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.205
Skin Sensitization:	0.345
Carcinogencity:	0.788
Eye Corrosion:	0.787
Eye Irritation:	0.769
Respiratory Toxicity:	0.974

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474748

Natural Product ID:	NPC474748
*Common Name:**	PDQCQIKOOSJLFX-XMLUMMTISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PDQCQIKOOSJLFX-XMLUMMTISA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9-4-5-11-13-10(9)6-12(17)15(13,8-16)7-14(11,2)3/h5,8-10,12-13,17H,4,6-7H2,1-3H3/t9-,10+,12?,13+,15+/m1/s1
SMILES:	CC1CC=C2C3C1CC(C3(CC2(C)C)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481259
PubChem CID:	21778025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	isolated from the marine red alga Polysiphonia	n.a.	PMID[15787444]
NPO32658	geniculosporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917307]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	0.0	mm	PMID[497095]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	10.0	mm	PMID[497095]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	0.0	mm	PMID[497095]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	0.0	mm	PMID[497095]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474748 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1343
0.2-0.3	8591
0.3-0.4	15663
0.4-0.5	7386
0.5-0.6	7059
0.6-0.7	2201
0.7-0.8	280
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8488	Intermediate Similarity	NPC328313
0.8452	Intermediate Similarity	NPC82902
0.8353	Intermediate Similarity	NPC474218
0.8295	Intermediate Similarity	NPC171441
0.8293	Intermediate Similarity	NPC7232
0.8276	Intermediate Similarity	NPC472483
0.8256	Intermediate Similarity	NPC94755
0.8256	Intermediate Similarity	NPC469994
0.8235	Intermediate Similarity	NPC329043
0.8235	Intermediate Similarity	NPC58841
0.8235	Intermediate Similarity	NPC321187
0.8235	Intermediate Similarity	NPC161423
0.8235	Intermediate Similarity	NPC227064
0.8193	Intermediate Similarity	NPC45495
0.8182	Intermediate Similarity	NPC24772
0.8182	Intermediate Similarity	NPC472971
0.8182	Intermediate Similarity	NPC472970
0.8182	Intermediate Similarity	NPC116146
0.8161	Intermediate Similarity	NPC472482
0.8161	Intermediate Similarity	NPC317590
0.8161	Intermediate Similarity	NPC472481
0.8161	Intermediate Similarity	NPC312215
0.8161	Intermediate Similarity	NPC472484
0.814	Intermediate Similarity	NPC179006
0.814	Intermediate Similarity	NPC474853
0.8111	Intermediate Similarity	NPC250575
0.8068	Intermediate Similarity	NPC294480
0.8046	Intermediate Similarity	NPC212843
0.8023	Intermediate Similarity	NPC473246
0.8023	Intermediate Similarity	NPC165064
0.8023	Intermediate Similarity	NPC214043
0.8023	Intermediate Similarity	NPC59453
0.8023	Intermediate Similarity	NPC85774
0.8023	Intermediate Similarity	NPC221758
0.8	Intermediate Similarity	NPC151519
0.7978	Intermediate Similarity	NPC76879
0.7978	Intermediate Similarity	NPC477943
0.7978	Intermediate Similarity	NPC2983
0.7955	Intermediate Similarity	NPC96496
0.7955	Intermediate Similarity	NPC472493
0.7935	Intermediate Similarity	NPC263347
0.7931	Intermediate Similarity	NPC471224
0.7931	Intermediate Similarity	NPC474083
0.7931	Intermediate Similarity	NPC36350
0.7907	Intermediate Similarity	NPC62214
0.7907	Intermediate Similarity	NPC476082
0.7907	Intermediate Similarity	NPC278648
0.7901	Intermediate Similarity	NPC199316
0.7901	Intermediate Similarity	NPC102313
0.7889	Intermediate Similarity	NPC320026
0.7889	Intermediate Similarity	NPC46281
0.7889	Intermediate Similarity	NPC191684
0.7889	Intermediate Similarity	NPC69622
0.7882	Intermediate Similarity	NPC136150
0.7865	Intermediate Similarity	NPC471724
0.7865	Intermediate Similarity	NPC183546
0.7865	Intermediate Similarity	NPC211162
0.7865	Intermediate Similarity	NPC471941
0.7865	Intermediate Similarity	NPC474854
0.7865	Intermediate Similarity	NPC53911
0.7865	Intermediate Similarity	NPC48866
0.7865	Intermediate Similarity	NPC183374
0.7865	Intermediate Similarity	NPC247406
0.7857	Intermediate Similarity	NPC261125
0.7857	Intermediate Similarity	NPC152061
0.7857	Intermediate Similarity	NPC181195
0.7841	Intermediate Similarity	NPC145879
0.7841	Intermediate Similarity	NPC20688
0.7841	Intermediate Similarity	NPC474778
0.7841	Intermediate Similarity	NPC474732
0.7841	Intermediate Similarity	NPC472494
0.7841	Intermediate Similarity	NPC472491
0.7841	Intermediate Similarity	NPC474733
0.7841	Intermediate Similarity	NPC51014
0.7841	Intermediate Similarity	NPC327115
0.7841	Intermediate Similarity	NPC31564
0.7841	Intermediate Similarity	NPC155011
0.7816	Intermediate Similarity	NPC472480
0.7816	Intermediate Similarity	NPC237712
0.7805	Intermediate Similarity	NPC313185
0.7805	Intermediate Similarity	NPC114236
0.7802	Intermediate Similarity	NPC154101
0.7791	Intermediate Similarity	NPC193347
0.7791	Intermediate Similarity	NPC46881
0.7778	Intermediate Similarity	NPC41217
0.7778	Intermediate Similarity	NPC310010
0.7778	Intermediate Similarity	NPC326627
0.7778	Intermediate Similarity	NPC54689
0.7778	Intermediate Similarity	NPC155479
0.7765	Intermediate Similarity	NPC157895
0.7765	Intermediate Similarity	NPC472478
0.7765	Intermediate Similarity	NPC104120
0.7765	Intermediate Similarity	NPC148685
0.7753	Intermediate Similarity	NPC474684
0.7753	Intermediate Similarity	NPC159046
0.7753	Intermediate Similarity	NPC58063
0.7753	Intermediate Similarity	NPC233836
0.7753	Intermediate Similarity	NPC167877
0.7753	Intermediate Similarity	NPC136548
0.7753	Intermediate Similarity	NPC142361
0.7753	Intermediate Similarity	NPC90652
0.7753	Intermediate Similarity	NPC187376
0.7753	Intermediate Similarity	NPC475740
0.7742	Intermediate Similarity	NPC472485
0.7727	Intermediate Similarity	NPC469948
0.7727	Intermediate Similarity	NPC202868
0.7717	Intermediate Similarity	NPC66429
0.7717	Intermediate Similarity	NPC470376
0.7717	Intermediate Similarity	NPC472942
0.7717	Intermediate Similarity	NPC152897
0.7717	Intermediate Similarity	NPC470375
0.7711	Intermediate Similarity	NPC215481
0.7701	Intermediate Similarity	NPC477373
0.7692	Intermediate Similarity	NPC123854
0.7692	Intermediate Similarity	NPC183283
0.7692	Intermediate Similarity	NPC2946
0.7692	Intermediate Similarity	NPC472476
0.7684	Intermediate Similarity	NPC147954
0.7674	Intermediate Similarity	NPC14151
0.7667	Intermediate Similarity	NPC477710
0.7667	Intermediate Similarity	NPC328539
0.7667	Intermediate Similarity	NPC471722
0.7667	Intermediate Similarity	NPC470417
0.7647	Intermediate Similarity	NPC477371
0.7647	Intermediate Similarity	NPC472490
0.764	Intermediate Similarity	NPC118648
0.764	Intermediate Similarity	NPC476043
0.764	Intermediate Similarity	NPC72133
0.764	Intermediate Similarity	NPC28252
0.764	Intermediate Similarity	NPC222613
0.764	Intermediate Similarity	NPC473168
0.764	Intermediate Similarity	NPC194417
0.764	Intermediate Similarity	NPC55309
0.764	Intermediate Similarity	NPC232156
0.764	Intermediate Similarity	NPC89077
0.764	Intermediate Similarity	NPC475022
0.764	Intermediate Similarity	NPC80590
0.7634	Intermediate Similarity	NPC111015
0.7634	Intermediate Similarity	NPC292793
0.7619	Intermediate Similarity	NPC197659
0.7619	Intermediate Similarity	NPC276769
0.7619	Intermediate Similarity	NPC74995
0.7614	Intermediate Similarity	NPC144258
0.7614	Intermediate Similarity	NPC470812
0.7609	Intermediate Similarity	NPC45269
0.7609	Intermediate Similarity	NPC23434
0.7604	Intermediate Similarity	NPC110149
0.759	Intermediate Similarity	NPC77501
0.7586	Intermediate Similarity	NPC477269
0.7586	Intermediate Similarity	NPC477271
0.7586	Intermediate Similarity	NPC477270
0.7586	Intermediate Similarity	NPC110780
0.7586	Intermediate Similarity	NPC129080
0.7582	Intermediate Similarity	NPC215029
0.7582	Intermediate Similarity	NPC474570
0.7582	Intermediate Similarity	NPC474245
0.7582	Intermediate Similarity	NPC84271
0.7582	Intermediate Similarity	NPC275740
0.7582	Intermediate Similarity	NPC77168
0.7582	Intermediate Similarity	NPC475921
0.7582	Intermediate Similarity	NPC268406
0.7582	Intermediate Similarity	NPC474704
0.7582	Intermediate Similarity	NPC170775
0.7582	Intermediate Similarity	NPC473999
0.7582	Intermediate Similarity	NPC472477
0.7582	Intermediate Similarity	NPC32830
0.7582	Intermediate Similarity	NPC476733
0.7582	Intermediate Similarity	NPC31985
0.7582	Intermediate Similarity	NPC309603
0.7582	Intermediate Similarity	NPC102414
0.7582	Intermediate Similarity	NPC472475
0.7582	Intermediate Similarity	NPC186688
0.7582	Intermediate Similarity	NPC86319
0.7582	Intermediate Similarity	NPC26959
0.7582	Intermediate Similarity	NPC1015
0.7579	Intermediate Similarity	NPC475894
0.7561	Intermediate Similarity	NPC234527
0.7561	Intermediate Similarity	NPC474140
0.7561	Intermediate Similarity	NPC14352
0.7556	Intermediate Similarity	NPC93778
0.7556	Intermediate Similarity	NPC134197
0.7553	Intermediate Similarity	NPC222845
0.7553	Intermediate Similarity	NPC45324
0.7553	Intermediate Similarity	NPC162001
0.7553	Intermediate Similarity	NPC469599
0.7553	Intermediate Similarity	NPC472932
0.7529	Intermediate Similarity	NPC82635
0.7529	Intermediate Similarity	NPC477514
0.7529	Intermediate Similarity	NPC477522
0.7529	Intermediate Similarity	NPC178852
0.7528	Intermediate Similarity	NPC470574
0.7527	Intermediate Similarity	NPC477520
0.7527	Intermediate Similarity	NPC206810
0.7527	Intermediate Similarity	NPC474807
0.7527	Intermediate Similarity	NPC470224
0.7527	Intermediate Similarity	NPC243866
0.7527	Intermediate Similarity	NPC233118
0.75	Intermediate Similarity	NPC477711
0.75	Intermediate Similarity	NPC477852
0.75	Intermediate Similarity	NPC263582

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	2050
0.2-0.3	4431
0.3-0.4	1732
0.4-0.5	399
0.5-0.6	211
0.6-0.7	154
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD3133	Approved
0.8235	Intermediate Similarity	NPD3665	Phase 1
0.8235	Intermediate Similarity	NPD3666	Approved
0.8023	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7791	Intermediate Similarity	NPD4221	Approved
0.7791	Intermediate Similarity	NPD4223	Phase 3
0.7778	Intermediate Similarity	NPD4753	Phase 2
0.7717	Intermediate Similarity	NPD4202	Approved
0.764	Intermediate Similarity	NPD5279	Phase 3
0.764	Intermediate Similarity	NPD3618	Phase 1
0.7614	Intermediate Similarity	NPD4197	Approved
0.7582	Intermediate Similarity	NPD5328	Approved
0.7528	Intermediate Similarity	NPD5329	Approved
0.75	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4697	Phase 3
0.7473	Intermediate Similarity	NPD6903	Approved
0.7444	Intermediate Similarity	NPD5280	Approved
0.7444	Intermediate Similarity	NPD4690	Approved
0.7444	Intermediate Similarity	NPD5205	Approved
0.7444	Intermediate Similarity	NPD4694	Approved
0.7444	Intermediate Similarity	NPD4688	Approved
0.7444	Intermediate Similarity	NPD4138	Approved
0.7444	Intermediate Similarity	NPD4693	Phase 3
0.7444	Intermediate Similarity	NPD4689	Approved
0.7444	Intermediate Similarity	NPD5690	Phase 2
0.7419	Intermediate Similarity	NPD6079	Approved
0.7396	Intermediate Similarity	NPD4755	Approved
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5210	Approved
0.7303	Intermediate Similarity	NPD4788	Approved
0.7273	Intermediate Similarity	NPD4692	Approved
0.7273	Intermediate Similarity	NPD4139	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD6083	Phase 2
0.7216	Intermediate Similarity	NPD6084	Phase 2
0.7188	Intermediate Similarity	NPD5695	Phase 3
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD7339	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7113	Intermediate Similarity	NPD5222	Approved
0.7113	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5221	Approved
0.7111	Intermediate Similarity	NPD5362	Discontinued
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7320	Approved
0.7079	Intermediate Similarity	NPD5369	Approved
0.7053	Intermediate Similarity	NPD5284	Approved
0.7053	Intermediate Similarity	NPD5281	Approved
0.7045	Intermediate Similarity	NPD4195	Approved
0.7041	Intermediate Similarity	NPD5173	Approved
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.703	Intermediate Similarity	NPD4754	Approved
0.7024	Intermediate Similarity	NPD4243	Approved
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.697	Remote Similarity	NPD5696	Approved
0.6961	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4634	Approved
0.6947	Remote Similarity	NPD4096	Approved
0.6932	Remote Similarity	NPD3617	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5332	Approved
0.6923	Remote Similarity	NPD5331	Approved
0.6915	Remote Similarity	NPD4518	Approved
0.6893	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD7128	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6893	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD6675	Approved
0.6893	Remote Similarity	NPD6402	Approved
0.6889	Remote Similarity	NPD4790	Discontinued
0.6882	Remote Similarity	NPD6098	Approved
0.686	Remote Similarity	NPD6926	Approved
0.686	Remote Similarity	NPD6924	Approved
0.686	Remote Similarity	NPD4784	Approved
0.686	Remote Similarity	NPD4785	Approved
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6809	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5133	Approved
0.6786	Remote Similarity	NPD3698	Phase 2
0.6782	Remote Similarity	NPD5275	Approved
0.6782	Remote Similarity	NPD4190	Phase 3
0.6778	Remote Similarity	NPD5368	Approved
0.6778	Remote Similarity	NPD4748	Discontinued
0.6778	Remote Similarity	NPD4252	Approved
0.6778	Remote Similarity	NPD7525	Registered
0.6774	Remote Similarity	NPD5363	Approved
0.6771	Remote Similarity	NPD5207	Approved
0.6771	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD6011	Approved
0.6762	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD6899	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5128	Approved
0.6737	Remote Similarity	NPD5737	Approved
0.6737	Remote Similarity	NPD5208	Approved
0.6737	Remote Similarity	NPD6672	Approved
0.6707	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4747	Approved
0.6706	Remote Similarity	NPD4244	Approved
0.6706	Remote Similarity	NPD4245	Approved
0.6705	Remote Similarity	NPD6933	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6701	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD6411	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6698	Remote Similarity	NPD6373	Approved
0.6698	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6435	Approved
0.6598	Remote Similarity	NPD5692	Phase 3
0.6596	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4695	Discontinued
0.6588	Remote Similarity	NPD4137	Phase 3
0.6588	Remote Similarity	NPD6922	Approved
0.6588	Remote Similarity	NPD6923	Approved
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5217	Approved
0.6574	Remote Similarity	NPD6869	Approved
0.6574	Remote Similarity	NPD6649	Approved
0.6574	Remote Similarity	NPD5216	Approved
0.6574	Remote Similarity	NPD8130	Phase 1
0.6574	Remote Similarity	NPD6650	Approved
0.6574	Remote Similarity	NPD6617	Approved
0.6574	Remote Similarity	NPD5215	Approved
0.6574	Remote Similarity	NPD5127	Approved
0.6574	Remote Similarity	NPD6847	Approved
0.6566	Remote Similarity	NPD6001	Approved
0.6549	Remote Similarity	NPD6054	Approved
0.6549	Remote Similarity	NPD6059	Approved
0.6531	Remote Similarity	NPD6050	Approved
0.6531	Remote Similarity	NPD5694	Approved
0.6531	Remote Similarity	NPD5693	Phase 1
0.6526	Remote Similarity	NPD4519	Discontinued
0.6526	Remote Similarity	NPD4623	Approved
0.6514	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD6053	Discontinued
0.6514	Remote Similarity	NPD8297	Approved
0.6512	Remote Similarity	NPD7143	Approved
0.6512	Remote Similarity	NPD4691	Approved
0.6512	Remote Similarity	NPD7144	Approved
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6101	Approved
0.6491	Remote Similarity	NPD6015	Approved
0.6491	Remote Similarity	NPD6016	Approved
0.6484	Remote Similarity	NPD6929	Approved
0.6477	Remote Similarity	NPD5733	Approved
0.6477	Remote Similarity	NPD4687	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4522	Approved
0.6455	Remote Similarity	NPD4632	Approved
0.6449	Remote Similarity	NPD5168	Approved
0.6442	Remote Similarity	NPD5091	Approved
0.6437	Remote Similarity	NPD7152	Approved
0.6437	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7150	Approved
0.6437	Remote Similarity	NPD5276	Approved
0.6437	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7151	Approved
0.6435	Remote Similarity	NPD6370	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data